[ CAS No. 74037-50-6 ] {[proInfo.proName]}

Name: 74037-50-6|3-Ethoxy-2-nitropyridine|98+%
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SKU: A995059
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Quality Control of [ 74037-50-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 74037-50-6 ]

Product Details of [ 74037-50-6 ]

CAS No. :	74037-50-6	MDL No. :	MFCD00006257
Formula :	C₇H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WBEVIQNYYGPESH-UHFFFAOYSA-N
M.W :	168.15	Pubchem ID :	52866
Synonyms :

Calculated chemistry of [ 74037-50-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.36
TPSA :	67.94 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	1.11
Log Po/w (WLOGP) :	1.39
Log Po/w (MLOGP) :	1.01
Log Po/w (SILICOS-IT) :	-0.5
Consensus Log Po/w :	0.89

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.75
Solubility :	2.96 mg/ml ; 0.0176 mol/l
Class :	Very soluble
Log S (Ali) :	-2.13
Solubility :	1.25 mg/ml ; 0.00742 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.93
Solubility :	1.97 mg/ml ; 0.0117 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.37

Safety of [ 74037-50-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 74037-50-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 74037-50-6 ]
Downstream synthetic route of [ 74037-50-6 ]

[ 74037-50-6 ] Synthesis Path-Upstream 1~5

1
[ 74037-50-6 ]
[ 6602-32-0 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 275,282

2
[ 74037-50-6 ]
[ 16867-03-1 ]

Reference： [1] Chemische Berichte, 1928, vol. 61, p. 1028

3
[ 74037-50-6 ]
[ 89943-11-3 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 275,282

4
[ 74037-50-6 ]
[ 10006-74-3 ]
[ 13269-19-7 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1953, vol. 72, p. 125,131

5
[ 74037-50-6 ]
[ 15128-82-2 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 4, p. 577 - 579

[ 74037-50-6 ] Synthesis Path-Downstream 1~45

1
[ 14773-50-3 ]
[ 74037-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid
	With sulfuric acid; nitric acid at -15℃; und folgenden 1-stdg.Erwaermen auf dem Wasserbad;

Reference： [1]den Hertog et al. [Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 275,282]
[2]Koenigs; Gerdes; Sirot [Chemische Berichte, 1928, vol. 61, p. 1028]

2
[ 74037-50-6 ]
[ 6602-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	With water; hydrogen bromide; acetic acid at 130℃; unter Druck;

Reference： [1]den Hertog et al. [Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 275,282]

3
[ 74037-50-6 ]
[ 10006-74-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With iron; ammonium chloride; acetic acid In ethanol at 80℃; for 1h;	89.2 [00358] Step 2. The nitro intermediate 89-B (6.0 g, 35.7 mmol) prepared in step 1 above was dissolved in a mixture of 50 mL of EtOH and 2 mL of acetic acid. Fe powder (10.0 g, 178.5 mmol) and NH4C1 (9.5 g, 178.5 mmol) were added. The resulting mixture was heated at 80 C with stirring for 1 h. The mixture was filtered and the filterate was concentrated in vacuo to a residue, which was dissolved in 100 mL of EtOAc. The organic solution was washed with H20 (100 mL x 2), then concentrated in vacuo to provide the amino pyridine 89- C as a yellow oil (3.2 g, 65%). 1H NMR (400 MHz, CDC13) δ: 7.65 (d, J = 4.8 Hz, IH), 6.88 (d, J = 7.6 Hz, IH), 6.59 (dd, J = 4.8 Hz, 7.6 Hz, IH), 4.68 (br s, 2H), 4.04 (q, J = 7.2 Hz, 2H), 1.44 (t, J = 7.2 Hz, 3H). LC-MS: m/z = 139.1 [M+H]+.
	With hydrogenchloride; tin(ll) chloride
	With hydrogen In ethanol at 40℃; for 3h;	20 Preparation 20; 3-ethoxy-2-pyridinamine Preparation 20 3-ethoxy-2-pyridinamine Hydrogenation of 3-ethoxy-2-nitropyridine (5.0 g, 30 mmol) in ethanol (150 ml) was effected over PtO2 in a Parr bottle at 40° C. over hydrogen (50 psi) for 3 h. The catalyst was removed by filtration, and the solvent removed in vacuo to give a brown gum which was extracted with boiling pentane to afford the title compound as a white solid (3.1 g, 22 mmol). mp 84° C.

With hydrogen

14 3-Ethoxypyridin-2-amine was obtained by hydrogenation of 3-ethoxy- 2-nitropyridine (synthesized as described for 2-bromo-3-methoxypyridine using 2- nitropyridin-3-ol and ethyl iodide) in the presence of PD/C. H NMR (CDCL3, 500 MHz) 5 7.64 (d, 1H), 6.89 (d, 1H), 6.59 (t, 1H), 4. 64 (bs, 2H), 4.05 (q, 2H), 1.44 (t, 3H).

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - WO2014/8214, 2014, A1 Location in patent: Paragraph 00356; 00358
[2]Koenigs; Gerdes; Sirot [Chemische Berichte, 1928, vol. 61, p. 1028]
[3]Current Patent Assignee: PFIZER INC - US2005/20587, 2005, A1 Location in patent: Page 17-18
[4]Current Patent Assignee: MERCK & CO INC - WO2005/21529, 2005, A1 Location in patent: Page/Page column 33-34

4
[ 74037-50-6 ]
[ 10006-74-3 ]
[ 13269-19-7 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1953,vol. 72,p. 125,131

5
[ 74037-50-6 ]
[ 89694-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	With water; hydrogen bromide; acetic acid at 125℃; unter Druck;

Reference： [1]den Hertog et al. [Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 275,282]

6
[ 74037-50-6 ]
2-chloro-pyridin-3-ol; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride at 130℃;

Reference： [1]Koenigs; Gerdes; Sirot [Chemische Berichte, 1928, vol. 61, p. 1028]

7
[ 74037-50-6 ]
[ 57883-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid at 130℃;

Reference： [1]Koenigs; Gerdes; Sirot [Chemische Berichte, 1928, vol. 61, p. 1028]

8
[ 74037-50-6 ]
5-Ethoxy-6-nitro-pyridin-3-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With O-Methylhydroxylamin; potassium <i>tert</i>-butylate; zinc(II) chloride In dimethyl sulfoxide Ambient temperature;

Reference： [1]Seko, Shinzo; Miyake, Kunihito [Chemical Communications, 1998, # 15, p. 1519 - 1520]

9
[ 74037-50-6 ]
[ 7425-45-8 ]
2-(5-ethoxy-6-nitro-pyridin-3-yl)-2-hydroxy-butyric acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With air; sodium hydride; benzaldehyde 1.) DMF, 0 deg C; r.t., 2.) DMF, r.t.; Yield given; Multistep reaction;

Reference： [1]Lawrence, Nicholas J.; Lamarche, Olivier; Thurrab, Nabil [Chemical Communications, 1999, # 8, p. 689 - 690]

10
[ 74037-50-6 ]
[ 12258-64-9 ]
[ 64-19-7 ]
[ 89694-54-2 ]

Reference： [1]Koenigs; Gerdes; Sirot [Chemische Berichte, 1928, vol. 61, p. 1028]

11
[ 14773-50-3 ]
[ 74037-50-6 ]

Reference： [1]Schickh; Binz; Schulz [Chemische Berichte, 1936, vol. 69, p. 2595] Koenigs; Gerdes; Sirot [Chemische Berichte, 1928, vol. 61, p. 1028]

Yield	Reaction Conditions	Operation in experiment
	at 130℃;

13
[ 74037-50-6 ]
[ 34851-41-7 ]
[ 909854-17-7 ]